CM's can usually only have Fastpasses for 4 days at one time, 7 days in advance. If she has a resort reservation on her
MDE profile she gets a 60 day window, and it may override the 4 day limit (we've never used guest passes this way) so that's why she can do her boyfriend's entire stay. Similar to how APs can only have 7 days unless they are staying on property, then it jumps to the length of stay. I think also, because you only have a 1 day reservation that when it checks for later days it doesn't see anyone in the party having an on property reservation (60 day window) or a ticket (which would give a 30 day window), so it defaults back to the 7 day window. It's weird to me that she can book the day before you arrive, but can't book the day you check out (are you sure the night you have booked is the day you THINK it is) because those 2 days should give her a 60 day window. She can get 2 days, but it doesn't seem like the right ones. The "reached allotment" is probably because some FP for the boyfriend's trip exist, but I don't know the intricacies of how it counts CM tickets. Does she have any other FPs for any other days?
Although, we have experienced screwy stuff with guest passes. Last Christmas, my husband and I were visiting with my Dad. So we were using 2 guest passes. One day my DH thought he lost his guest pass so I tried to transfer our existing FP to include the 3rd guest pass that was at home. It kept telling me that the guest pass limit had been reached. But we only had 2 days worth of FP on 2 guest passes and never used the 3rd one at all. Once ALL FPs had expired, then it let me book additional days on all three. But my Dad has also experienced problems where his FPs were deleted (but the guest ones stayed) or everyone's were deleted.
Unfortunately, these are the downsides of the free admission. I don't think she is going to be able to book rolling fastpasses this far out. Every time we've traveled with a friend, my Dad's "extra time" has ended on their checkout date. (So I think it's better to have the one day at the end of the trip not the beginning, but we've never tried that) Additional linked tickets can change the math. We've noticed whenever we have a party ticket in our accounts my Dad can make FPs for 5 days. I assume comp tickets also change things up, but we've never tried it. But the "4 in 7" is a big problem when staying off-site and the main reason we have all soured on WDW. Free is great, but when every new attraction is unavailable without a lot of work refreshing, it sucks the fun out.
EDIT: Our next trip is with a friend whose vacation ends 8/31. But yet I checked my Dad's MDE and he CAN make FP for 60 days including past friend's trip (assuming she is in the booking party). So I don't know!
